Wow @Bear77 that is some list. I think because you offered an exhaustive list of losses in the worst stock Forum post, you are well within your rights to do the same for the wins!! Ditto for you @SudMav nice gains mate.

I think in fairness to my losses being limited to only 2 x worst case scenarios (which were total losses of ~$20-30K each) when I have many other losses between $5K - $20K that did not totally tank, and as an effort to keep my investing ego in check (funny how we remember all those wins but somehow avoid the losses like a plague) I might just stick to 2-3 best investments here.

My winner theme here is to buy and hold if you love the company and that is certainly the case for the first 2:

1. I purchased Cochlear when I was struggling to find some extra money in early 2004 500 shares @ 20.88/share + $33 brokerage (bloody Commsec) and still have the same holding plus some SPP shares gathered during the capital raise during Covid (another 205 @ $140/share). Can you believe I was so hesitant to do the initial purchase as I had never paid $20 for a share at that stage, but everything said they were a brilliant company and frankly, still are, but maybe were overpriced until the latest price adjustment. So, including dividends to date ($33K) including Franking credits, just a tad under $200K total return right now.
2. Data#3 I purchased at IPO in 1997 2000shares @ $1.25/share. In 2011 they did a 10:1 stock split meaning I then had 20,000 shares at a purchase price of $0.125/share. I eventually sold some shares after doing DRP for years in July 2020 for $5.50/share. Funnily enough I then decided to get back in in December 2020 (so 6 months later} when they had dropped to $5.30/share as I still thought they still had distance to travel, and I hadn't done much with the funds from the previous sale. So, including dividends to date ($58.6K) including Franking credits, $239K total return right now.
3. Last one is for fun and very similar to @Bear77 for Sirtex, something a broker guided me into in Mar 2002 getting 2000 shares @$1.91/each and as @Bear77 identified, they were a takeover target and paid $33.60/share on exit so $63,300 profit over 16 years or a 16 bagger in old parlance.

Some shares were simply milked for dividends and Telstra was a great example. Any time they offered an off market buy back where there was a large capital loss along with a large, franked dividend, I jumped at it. I don't hold any TLS these days but from IPO in 1999 to 2022 I show a capital loss of $14.7K and a total dividend including franking credits of $234K or a total return of $219K. You don't always have to hold purely for capital gain, although there would have been some growth if I didn't continually take the off market buy back bargains!

So, enough bragging as I have many more losers than winners, but with the right companies and a lot of time, good things are possible.

Note: this edit is due to seeing @Bear77 footnote regarding Sharesight reporting dividends as Grossed up dividends including franking credits. Sorry, just started using Sharesight in August and didn't realise this was the (unusual) case. Comments regarding dividends above have now been corrected!!

01-Oct-2024: In dollar terms, my best total returns (capital gains plus dividends combined) from real money positions in real life portfolios have come from the following - from best to tenth best:

Note total returns are dividends added to capital gains less capital losses, and it appears that Sharesight have included the value of the franking credits in those dividend returns.

1. MND, Monadelphous Group - no longer held, but held them for over a decade and kept loading up at lower levels and trimming them at higher levels - they were by far my best ever investment. $145K total return over 3 portfolios.
2. NWH (NRW Holdings) - still holding them in my super, have held them since December 2012, but got out in January 2014 and got back in at $1.26/share in October 2017 and have held them ever since - now around $3.58 (yesterday's close). More on them below. $118K total returns so far. (currently in 1, but formerly in 3 portfolios)
3. CDA, Codan, $100K total return, across three portfolios
4. NST, Northern Star, held since August 2012, paid just $0.935 for my first tranche. Closed yesterday at $15.97 and were over $16/share last week. Total return across three portfolios has been $97.5K so far.
5. GNG, GR Engineering Services, $96.5K in total returns so far (still held) and quite a bit of that via fully franked dividends (across two portfolios).
6. AX1, Accent Group, formerly RCG Corporation when I started buying them back in early 2011 at prices in the low 50 cent zone (50.5 to 53.5 cps), then doubled down at 34.5 to 35 cents and then doubled down again at 37 cps during April through August 2012, they paid excellent dividends and when I sold out of one portfolio they were $1.45 and I sold out at $1.336/share in the other one - both in May 2018 (they closed at $2.38 yesterday, but I no longer hold them). My total return for RCG/AX1 was $82.5K across two portfolios.
7. FMG, Fortescue, formerly Fortescue Metals Group, no longer held, $62K across three portfolios
8. LYL, Lycopodium, still held, $49K total return so far, quite a bit of it via dividends, via two portfolios.
9. ARB, ARB Corporation, $48K total return across three portfolios, not currently held.
10. SRX, Sirtex Medical, discussed yesterday (more below), $46K total return, one portfolio.

In dollar terms the ones that followed those (at #11 to #33) were WAM (mostly gains made a decade ago with WAM), MAQ, MLD (MACA, have been acquired, no longer ASX-listed), ALU (Altium, been acquired, no longer ASX-listed), TNE, RFF (Rural Funds Group), IGO (then known as Independence Group, years ago), NCK, BPT (Beach Energy, years ago, up until Seven Group took a large stake in them and organised the merger with Drillsearch), CSL, PTM (Platinum Asset Management, back when Kerr Neilson was still running it), UWL (Uniti Group, were acquired), EVN, PMV, RHC, WMI, MIN, WLE, CZZ (Capilano Honey, were acquired), ABB, JIN, EGL & WAX. Below WAX at #33 we're talking about total returns of less than $15K, so not so material. Most of the WAM Funds LICs (WAM, WMI, WAX and WLE) gains were made in the earlier years, not recently.

Of those 33, the only ones I hold today are NWH, GNG, LYL, NST, WLE in real life. Here on SM I hold those 5 plus CDA, ARB, MAQ and EGL at this point in time (from those 33).

In percentage terms, the following have provided the best bang for my bucks, however because some of them were smaller positions, a lot of them did not provide the best total dollar returns compared to my larger positions:

1. S2 Resources (S2R), +255.61% p.a., I was issued these when IGO acquired Sirius Resources to get hold of their Nova nickel mine, and I bought some more, then sold out reasonably soon afterwards when they spiked up on some drilling results.
2. Uniti Group (UWL), +91.57% p.a. Would have been higher if I'd waited another couple of weeks for that takeover offer that came.
3. Macquarie Technology Group (MAQ, formerly Macquarie Telecom), +74.31% p.a. I wish I still held this company. They stopped paying dividends years ago, so the vast majority of these gains have been capital gains.
4. WAM Microcap (WMI), +71.64% p.a., I participated in the IPO (because I already held WAM and WAX at the time) and they had a great run up at their start, which is where I made those returns. They also paid good dividends which grew every year.
5. Staverley Minerals (SVY), 69.2% p.a. - I got into this one when Chris Cairns started it up after selling his previous gold company, Integra Mining to Silver Lake Resources for A$426 million (45.2 cps) being a 43.6% premium to Integra's closing price of A$0.315 on 3rd August 2012, the day before SLR's offer was lobbed in, and a 40.3% premium to Integra's 20-day VWAP of A$0.307. This was when I first realised what a muppet Luke Tonkin at SLR was (he's now the MD at Vault Minerals, VAU, having engineered a reverse takeover of Red 5 and then got the company name changed to Vault). That was WAYYYY too much to pay for Integra!! I rode Staverley (SVY, Chris Cairns' new company at the time) up from 20c to 60c/share in 2014 and then sold out when they started dropping on boring / dud drilling results - my call was the hype was coming out of the stock, and I got that call right.
6. Globe International (GLB), 63.62% p.a. - A momentum play during Covid (2nd half of 2020, and through 2021).
7. Capilano Honey (CZZ), 62.99% p.a., another momentum play, plus Wroxby Pty Ltd, a private investment company controlled by Kerry Stokes and his son Ryan owned 17% of CZZ when I bought in, and CZZ were then acquired after a bidding war between two suitors during which time Wroxby increased their stake to 21.6% of CZZ - see here: https://www.afr.com/companies/stokes-says-takeover-offer-is-sweet-deal-for-all-capilano-shareholders-20180913-h15bqk - At the time I was having some success looking at some of lesser-known companies that WA's billionaires were investing their own money in - and sometimes following them in. This was a good example of a positive outcome from that strategy.
8. Sirtex Medical (SRX), 62.21% p.a. - further details below (also discussed yesterday).
9. Jumbo Interactive (JIN), 61.79% p.a. - not held for a long time, just a good time. I got out of JIN because of overseas expansion risk alongside the risk that I thought that Tatts dot com (now https://www.thelott.com/) presented by offering the same Australian lottery tickets at a lower cost than what JIN's site was offering them for. I switched to Tatts, now "the Lott", and have never gone back to JIN's https://www.ozlotteries.com/ site for my own family's ticket purchases. At the point that I sold, I could not clearly identify JIN's competitive advantage here in Australia. Still can't. Looked like the market agreed with me when their SP dropped from $27 to $7 (-74%) in the 5 months from October 2019 to March 2020, but they've been recovering since then. Now $13.70. I sold out at $2.32 in December 2012 after buying them 3 months earlier at $1.38 (first tranche) and $1.12 (2nd tranche). I'm glad I didn't follow them after that - I would have hated to see that rise up to $27 after I sold out at $2.32.
10. Accent Group (AX1, formerly RCG), 61.64% p.a. - see above list for details.

In percentage terms, the next 5 after that were ABB (57.37% p.a.), ALU (52.07% p.a.), NEA (Nearmap, 51.78% p.a.), WTC (51.11% p.a., WiseTech was another one I sold out of way too early) and BPT (50.15% p.a., Beach Energy, formerly Beach Petroleum, another Adelaide-HQ'd company, was another one I got interested in because of Kerry Stokes' involvement). Speaking of which (as in bombed-out Energy sector companies based in Adelaide), I added Santos (STO) to my SMSF @ the $7.00 opening price this morning - also where they closed, bang on $7. Capex reducing in the current FY and even further next year, much better balance sheet than a few years ago, and involved in multiple gas projects both in Australia and overseas. Also STO are Australia's second largest energy sector company after Woodside, and I don't currently like Woodside much. So my direct exposure to Australia's energy sector is now via COE (Cooper Energy) and Santos (STO).

Finally, some people talk about yield traps, meaning companies that people buy for their high dividend yields and still lose money on because of capital losses. That can happen, but not always.

Here are my 22 best companies in order of dividend yield (which includes the value of the attached franking credits, so they are grossed up yields), and I've also included my capital gain/loss percentages, and finally the total shareholder return percentages (which are the previous two numbers added together) - all are p.a. (per annum) percentages:

Notes:

1. The companies listed in blue were held in just one of my portfolios, the others were held in either 2 or 3 portfolios and the figures are for the combined holdings across those portfolios; the ones in italics are no longer listed on the ASX, in all cases because they were taken over by another company except Brierty who went in VA in 2017 and then were liquidated, after I sold out of them;
2. The SRG referred to there (at the bottom of that screenshot) was the "old" SRG before their merger with GCS (Global Construction Services) when they were still known as SRG Ltd; it's misleading because GCS acquired SRG (a reverse takeover of GCS by SRG), then changed their own name from GCS to SRG Global - and are still trading today as SRG Global with the ticker code SRG - but those numbers refer to the old SRG Ltd prior to that merger, and Sharesight should be calling them SRG Ltd, not SRG Global Ltd which is the name of the new SRG. The new SRG has the old SRG management (David Macgeorge as MD,) because it was a reverse takeover, but I'm providing excessive detail now; short version is: Those numbers refer to SRG before the merger with GCS;
3. Tribune (TBR) and Rand (RND) were controlled by the same people - and had very similar Boards (in terms of the same directors) - and a complaint was lodged with the Takeovers Panel (TOV) regarding the true owners / controllers of both companies not providing adequate disclosure as per the ASX rules about their ownership / control of the companies, and TOV made a declaration of unacceptable circumstances in relation to the true ownership and control structure of both companies (who had shareholdings in each other similar to the arrangement between SOL and BKW plus a series of interconnected holding companies as substantial holders) and both companies suddenly decided to sell up millions of dollars worth of gold bullion that they had stored in the Perth Mint (which had been recorded in their books at cost, not market value, thus making the companies look like they were worth far less than they really were) and to also pre-pay a bunch of tax to generate franking credits, so that they could each provide their shareholders with an immediate massive fully franked special dividend. I knew their share price would fall a LOT when they went ex-div, but I took the plunge and invested in both companies to get those special dividends and kept those positions for 45 days to become entitled to the franking credits as well (the 45 day rule). They then both brought forward the payment date of the special dividends and I got them both very quickly. I don't trust their management, so don't normally invest in either of them, but that was a special situation where the major owner was getting his share of that gold that those companies held in the Perth Mint out of the companies via the special dividends before he was forced to relinquish a bunch of his shares because of the upcoming TOV orders, which is what did happen. You can make money on those two if you are very nimble and/or lucky, but it's not a company where the management is particularly interested in returns for their ordinary shareholders, so beware. I lost a small amount on TBR but made enough money on the RND trade to make both worthwhile for me. RND is a very low liquidity company, so it could have been a lobster pot, but there was increased market interest in the two companies at that time (because of the massive special dividends and their Perth Mint gold being sold and the TOV Panel proceedings and orders) so I was confident I'd be able to get out, and I did. It's not something I do often, but it was right there in front of me...;
4. Talisman (TLM) was another special situation where I was lining up to get their special dividend and a capital return after Sandfire (SFR) paid TLM for the land (tenements) that contained the Monty copper/gold project near Sandfire's De Grussa copper/gold mine. They paid a 6.375 cps fully franked special dividend in December 2018 followed by a 15.625 cps capital return in March 2019. I wasn't interested in owning any TLM shares after that;
5. IPE was called ING Private Equity Access Fund when I invested in them and later changed their name to IPE Ltd, and then were acquired by Mercantile OFM Pty Limited in 2018 (for 7.75 cps) - and Mercantile OFM (a private company) was deregistered by ASIC earlier this year after they lodged a request for voluntary deregistration, probably because they'd been acquired by another private company or PE mob;
6. Sirius (SIR) was another special situation where I was holding them for their takeover by IGO who were then known as Independence Group Ltd. IGO acquired SIR in late 2015 for 0.66 IGO shares and A$0.52 cash per Sirius share plus SIR shareholders received one S2R share for every 2.5 Sirius shares held. You can see above (in the list of best percentage total returns, not the screenshot directly above but the list above that one) that S2R provided my best return in percentage terms (+255.61%), plus IGO provided me with my 18th best total shareholder return in dollar terms, mostly via capital growth, so if you take IGO, S2R and SIR together, I did well out of them, despite the capital loss on SIR;
7. Verbrec (VBC) was known as LogiCamms when I held them and made money on them. I sold out well before that name change; and
8. These numbers represents snapshots in time - being different periods when I was invested in those companies in either one, two or three of my portfolios, so the total shareholder returns are for me only for the periods that I held those companies - some of them are still trading but I haven't been invested in the majority of them for years.

I have to cook some Mexican now. Taco Tuesday. Back in a while.